


When You Least Expect It

by fanboi214



Series: When You Least Expect It A [1]
Category: Arrow (TV 2012), Lost Girl, Supernatural
Genre: Crossover, Crossover Pairings, M/M, Multi, Multiple Crossovers
Language: English
Status: In-Progress
Published: 2014-01-10
Updated: 2014-10-17
Packaged: 2018-01-08 05:10:16
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 2,979
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1128714
Author URL: https://archiveofourown.org/users/fanboi214/pseuds/fanboi214
Summary: <blockquote class="userstuff">
              <p>When You Least Expect It<br/>Fandoms: Supernatural, Lost Girl, Arrow.<br/>Pairings:Dean/Bo/Ryan,<br/>Ratings: NC-17<br/>Warnings: M/M, Could have some dub-con in the future.<br/>Synopsis: When Dean and Sam have to find a incubus loose in Starling City, Dean calls in an expert on the subject.<br/></p>
            </blockquote>





	1. What Sammy Doesn't Know

"Oh fuck! Fuuuuuuuuck! I’m gonna cum,” Dean Winchester’s voice rang out through the rafters. Dean wasn’t normally vocal in bed, but then again nothing was ordinary about sex with a succubus. And Bo was beginning to realize that sex with the young hunter was quite unusual in its own right. Being a succubus Bo was used to doing most the heavy lifting in her sexual encounters, but Dean was an incredibly spirited partner. He knew all the spots to stroke, exactly the way the thrust and his kiss... that kiss could nearly bring a woman to orgasm on its own. His enthusiasm was incredibly impressive especially give the... circumstances. Yes, Dean Winchester truly was a sexual being even if entirely human.

Dean lay beneath the sheets panting in post coital glow, “I’m not gonna die now, right?”

Bo let out a light chuckle, her fingers lightly drifting up and down his arm. “No. Your chi will restore itself in a little while. I only took a tiny bit, not that you made it easy for me.”

“What’s that mean?” Dean asked, propping himself up on his elbow and turning on his side to study her hypnotically beautiful figure.

“I could’ve accidentally drained you dry easily. You make it hard to focus on thinking. You’re a very... primal lover,” Bo clarified.

As Bo spoke another hand was snaking around Dean’s hips. The hand ghosted up Dean’s chest applying a tantalizing trail of pressure. The fingers slid up his chest towards his shoulder, where they came to rest. It was a nimble touch but still strong and assertive. It was a man’s touch, a man’s hand. When Ryan’s palm reached Dean’s shoulder his hand flattened, pressing Dean onto his back. “Especially those lips,” the brunette cooed as he pressed his mouth to Dean’s. They let out a muffled moan as their mouths collided and Ryan slid his naked form closer to Dean, pinning the man more tightly between him and Bo. As Ryan came up for air he had an adorable smirk. “I refuse to believe that last night was the first time you kissed another man,” He said.

“Honest to God truth,” Dean said with a nod.

“Not with your prowess,” Ryan insisted.

“Well I assume Bo had a bit to do with that,” Dean turned his head to nuzzle the succubus.

“Don’t look at me,” she replied. “Succubus can amplify lust, direct it here and there, but what you do with it is all you. Besides I hardly used my powers when you two were involved.”

“Guess I’m just a natural then,” Dean cooed.

Ryan smiled across at his mysterious and lovely girlfriend, well not quite girlfriend, and asked “Can we keep him?”

“Afraid I’m only on loan.” Dean replied with a smirk.

“Then lets at least make the most of you before we have to give you up,” Bo replied.

Dean glanced over to the clock on the mantle. He thought a minute and shrugged “I’ve got time.” With that the three disappeared beneath the sheets once more. Dean did have time. By his calculations he had two thousand two hundred and five hours, fifty two minutes and twelve seconds until the hounds of hell would come hunting for his soul and tear him from this Earth. Damn it, he was going to make good use of every last second. It had never really occurred to him that making use of that time might lead him to a threeway with another man and a monster, but dying had a strange way of putting things in perspective. Why not try everything once? He was relatively unclear of how the succubus’s boyfriend got involved in all this, but turns out he quite enjoyed it, and he could successfully cross having sex with a succubus off his bucket list.

**FIVE YEARS AND MANY RESURRECTIONS LATER**

“I’m surprised you’re not more excited,” Sam called out from the motel bathroom as he fought to gel his massive mane into something that looked somehow hip. 

“We’ve never come across a succubus before. Super hot, sex-loving lady demon. Seems right up your alley.”

“Sammy, I hope you’re not implying I’d ever be anything less than professional,” Dean replied from the bedroom, where he was struggling to get a pair of skinny jeans up over his rather ample ass.

“Just promise me you won’t have sex with her. Remember we’re here to stop it, not feed it.”

“Oh, one small thing I forgot to mention. I talked to the victim’s ex-girlfriend, Ashley.” Dean shouted.

“Yeah?” Sam replied finally feeling at peace with his hair. He took a step back to review himself in the mirror. In a pair of slacks and a form fitting button up, he thought he was adequately dressed to catch the eye of any succubi.

“She’s a dude.”

“What?” Sam’s head came popping out of the bathroom, his mouth slackjawed in confusion and shock.

“Victim didn’t have an ex-girlfriend,” Dean said finally getting the pants zipped and rising to his feet. “He had an ex-boyfriend. He was gay. So I’m thinking our succubus is more of an incubus, and a gay one at that.”

“Oh...” Sam said quietly as he processed the new information. “Well... okay then.” He blinked a bit. “Is Verdant a gay club then?”

“Not as far as I can tell. Guess our boy just likes hunting in a run of the mill club. So the stake out plan is still solid, just keep your eyes on the guys.” Dean replied.

“You’re taking this surprisingly well,” Sam replied a little surprised and impressed by his brother’s openmindedness. “Though you look like an idiot.”

Dean frowned and looked down at his outfit. He was rocking a deep V-neck shirt with some hip hugging skinny jeans and 90s style spiked hair. “Aren’t you supposed to look like an idiot when you’re going to a club.”

“Not like that,” Sam shook his head.

“Whatever,” Dean grumbled “I bet more guys hit on me than you sasquatch.”

“If you say so,” Sam rolled his eyes “Well at least now I won’t have to worry about you trying to sleep with it.” Dean simply suppressed a smile.

***Meanwhile***

“Who’s Dean Winchester?” an inquisitive Kenzie called out from the couch before Bo was even able to get entirely into their apartment.

“What?” Bo replied befuddled.

“Bo-Bo, we’re supposed to be besties. You can’t be leaving me out of the boy gossip.” Kenzie said hopping to her feet.

Bo waved off her pint sized sidekick and disappeared into the kitchen. “Sorry, Kenz. That’s old news. I hooked up with Dean years ago when I was still doing the whole bad girl thing with Ryan.” Bo remerged from the kitchen sipping a glass of water. “It doesn’t matter anyway, he’s dead now.”

“Wrong-o. Unless the dead of learned how to dial out and leave weirdo vague messages on our machine, which considering some of the stuff we deal with isn’t entirely improbable.” Kenzie replied with a hint of reflection.

“Wait he’s alive?” Bo said surprised. “I think I got duped.”

“Do we hate him?” Kenzie asked “I’m so ready to hate him. Faking your death is a major faux pas, especially if you’re going to call after.”

“He didn’t exactly fake his death,” Bo said “But he told me he was dying. He said having sex with a succubus was like a dying wish,” She sighed. “I don’t know I was hungry. He was cute. It seemed like a good idea at the time.”

“Oh!” Kenzie cried “He knows about the whole succubus shabang? That makes the message make so much more sense. He said that he thought there was someone ‘like you’ in Starling City, California and he wanted your help teaching them how to ‘control themselves.”

That certainly got Bo’s attention. “You don’t think... Another succubus?” Bo bit her lip. “Outside of my mother, I’ve never met another succubus. If we’re as rare as the Fae say this might even be another relative.”

“Road trip!” Kenzie squealed running off to pack a back.


	2. Two Hunters, A Superhero, and an Incubus walk into a bar.

**Summary for the Chapter:**

> Sam and Dean begin their plan to stake out Verdant for a possible Incubus sighting.

"Look at him dressed like a normal person. It's like seeing a penguin on rollerskates, just weird," an unusually bemused Oliver whispered to Diggle. The he in question was assistant district attorney Adam Donner, who Laurel had drug to Verdant. Adam felt just as uncomfortable, as he appeared, however Laurel had insisted that he take at least one night off and join her. Out of his normal suit and tie, Adam was wearing a simple T-shirt which showcased his all too seldom seen chest quite nicely. 

"Focus, Oliver, we're on a mission," Diggle gritted. 

"Yeah, a mission to find a possible mad person who is possibly killing people in God only knows what way if he does actually exist," Felicity chimed in over the earpiece hidden in Oliver's ear. 

"We have discussed this. Three people murdered the night they leave my club is more than a coincidence, especially in Starling City." Oliver replied swiftly. 

"Then this is beyond dangerous. You don't know who you're looking for. You don't know why they killed these people. And you don't know how." Felicity emphasized. 

"Diggle and I will be perfectly safe, Felicity. We're just upstairs." Oliver reassured. 

Meanwhile Dean and Sam had made their way to the bar. Dean took out his phone and glanced down. "What are you waiting for?" Sam asked confused. 

"What?" Dean said nonchalantly. 

"You've checked that phone like ten times since we left the hotel," Sam said. 

"Just waiting to hear from someone." Dean replied. He had no clue if Bo would respond or if she'd even remember him. So far there'd been no reply. 

"Focus on the Incubus, Dean." Sam chastised. 

"Fine," Dean said. "How are you supposing we find him?" Dean asked. 

"That'll be easy," Sam said "It's whatever guy you're attracted to." 

"Come again?" 

"Calm down. Incubi and Succubi have a supernatural sexual effect on everyone regardless of your gender or preferences. Which makes it easy for straight guys like us, because the Incubi will be the only man we find sexually appeal." 

"You, uh, don't say," Dean said before taking a nice long swig of his drink.

"Don't freak out over it. It's not like some sort of hypnotizing pull. You'll just think he's kind of cute." Sam rolled his eyes. "Listen, I'm going to start in the front of the club. You keep an eye on the back half." 

As Sam parted, Roy Harper swung by wiping down the bar and Dean took a long survey of the men in this club. Finding a man he was attracted to in this crowd would be extremely easy, unfortunately that made finding an incubus incredibly difficult.


	3. Stake outs and shake ups.

**Summary for the Chapter:**

> The Winchesters move forward with their plan to stake out Verdant for a gay incubus. Little did they know that Team Arrow was planning a stakeout the same night.

Oliver and Diggle had made a solid round of the club. While Ollie had spotted many many questionable life choices he hadn't seen anything that really could be responsible for the string of murders. “Have you managed to spot... whatever it is you’re looking for,” Felicity chirped in their ears. Safely stationed in her normal spot in the ‘Arrow Cave’ 

“Maybe,” Oliver replied, with a glance back to Diggle. Diggle nodded, hanging back as Oliver made the approach to a rather tall man who was roaming through the club. Sam had a particular look in his eye as he swept the crowd, the kind of steady determined look a person got when they’re on a mission. 

“Find it?” Oliver called out as he stepped up behind Sam. 

“Wh-” Sam was taken completely off guard. He turned on his heels to see the man behind him. Fumbling a bit he spit out “Find what?”

“Whatever it is you’re looking for,” Ollie replied with a smirk.

“I’m not looking for anything,” Sam replied. His eyes flitted over this strange man who had approached him. He could be a incubus, right? Did he feel attracted to this man? The guy was built, that was for sure. His face sexy in a stubbly scruffy man’s man kinda way. Yeah, he was hot, and more important than that Sam thought he might even be feeling a little attraction to him. 

“Well now you’re just lying,” Ollie shook his head. “Everyone who comes to a place like this is looking for something.” 

Roy Harper cast a sideways glance down down the bar as he wiped it down. With as much subtlety as he could manage, Roy tried to get a read on the man at the end of the bar. Even without really interacting with him, Roy could tell he was an unusual and yet intensely interesting guy. Roy would place him somewhere in his mid-thirties but he had the rough world worn look of a much older man. Oozing with masculinity and confidence the man, Roy could swear that the man was checking him out. Try as he might he couldn’t catch the man staring though, it was almost as if he was intentionally drawing Roy in to see if Roy would hit on him. He cocked his head to the side with a ghost of a smile and looked over at Roy... or past Roy as he downed his scotch. Fuck this dude was hot, and judging from that ridiculous hair he was gay or at least curious. 

As Dean slammed his drink on the bar, the cute barback made his way over, with a bit too much pep in his step. “I’ll take that from you,” Roy offered before lifting the glass and wiping down the counter beneath it. Dean still wasn’t sure whether the kid was an incubus or just unreasonably attractive, but he’d gotten him to engage which was the first part of figuring out the answer to that question. 

“Should I let you touch that. I don’t want to get in trouble for giving alcohol to minors,” Dean quipped with a grin. 

“Don’t worry,” Roy replied. “Looks like you managed to down every last drop.”

“So you are a minor?” 

“I’m eighteen,” Roy said retorted somewhat defensively. 

“Thank, God,” Dean chuckled “Otherwise I’d have to feel awfully guilty about the thoughts I was having watching you back there.” 

That brought a smile to Roy’s face. Leaning on the bar he raised an eyebrow. “Oh? And just what kind of thoughts might those be?” 

“You know, they’re kind of hard to explain, but if you want I think I can show you.” Dean teased. 

“And my girlfriend, would she be allowed to view this demonstration?” Roy said with a wink.

“Girlfriend?” Dean looked surprised. “And here I thought we played for the same team.” 

“Who says that we don’t?” Roy smirked. “You seem like a man of... diverse tastes.” 

Dean chuckled, mentally reminding himself that this man was possibly a demon sex murderer. It was then he heard a high pitch squeal, “Dean Winchester?” 

He turned in his seat to find a petite girl with jet black hair and heavy eye liner. “Do I know you?” To his surprise he was met with a swift slap across the face. 

“That is for lying to Bo-bo.” Kenzie mouthed off. 

Dean didn’t have a minute to process what she said. His face still stinging from the slap as his eyes drifted up to notice the woman behind her. Gorgeous as ever the succubus had a grin from ear to ear. “You’re looking awfully spry for a dead guy,” Bo said plopping down next to him at the bar. 

“Well a good resurrection or three will do that to you,” Dean said still nursing his cheek a bit and giving Kenzie a glare. 

Roy stood there slackjawed with the momentarily dazed look a man tends to get when they first set their eyes on a succubus. He didn’t look like he really absorbed any of the commentary, which was good. Dean wondered if an incubus would have this kind of reaction to a succubus. Maybe the hot guy was just a hot guy. When Roy finally blinked back to reality he just looked from Bo to Dean. “You and her...” 

Dean gave him a wink. “What can I say? Guess I am a... how did you put it man of diverse tastes.” 

Over by the doorway, John Diggle maintained his location. He kept a careful eye on Ollie’s discussion with the unknown man he was interrogating. So far he didn’t seem anything out of the usual. However his guard position was soon put in jeopardy, as a rather enchanting woman in her late twenties made her way over to him. Without a word she began dancing on him, John tried to tactfully excuse himself from the situation, but his admirer was quite persistent. As she ground against him her face lining up to his own, Diggle cleared his throat. “Excuse me, I can’t...” 

“Come on,” she moaned “You’re hot and I’m sooo horny,” 

Diggle was shocked by her brazenness, but quickly distracted. His whole body felt a jolt of arousal hit him at once. His heart raced, his breathing increased and the bulge in his pants suddenly got a lot tighter. Diggle couldn’t help but notice how amazing this woman felt pressed to him or how pretty the eyes were batting up at him. “I can’t...” he panted trying to remind himself he was here to watch Oliver’s back. 

“Go for it man,” There was a soft whisper in his ear “I know you want to.” It was a voice that Diggle barely even registered. Had he been paying more attention he might’ve noticed he had heard it before. He might have felt the brush of fingertips on his neck before his burst of arousal. But he didn’t. He couldn’t control his impulses, and as he let this woman drag him out on to the dance floor he certainly didn’t notice the ‘deceased’ Tommy Merlyn slip out the door he was supposed to be guarding.


End file.
